Tropane and related alkaloid skeletons via a radical [3+3]-annulation process

Author:

Colson Eloïse,Andrez Julie,Dabbous Ali,Dénès FabriceORCID,Maurel VincentORCID,Mouesca Jean-MarieORCID,Renaud PhilippeORCID

Abstract

AbstractTropanes and related bicyclic alkaloids are highly attractive compounds possessing a broad biological activity. Here we report a mild and simple protocol for the synthesis of N-arylated 8-azabicyclo[3.2.1]octane and 9-azabicyclo[3.3.1]nonane derivatives. It provides these valuable bicyclic alkaloid skeletons in good yields and high levels of diastereoselectivity from simple and readily available starting materials using visible-light photoredox catalysis. These bicyclic aniline derivatives are hardly accessible via the classical Robinson tropane synthesis and represent a particularly attractive scaffold for medicinal chemistry. This unprecedented annulation process takes advantage of the unique reactivity of ethyl 2-(acetoxymethyl)acrylate as a 1,3-bis radical acceptor and of cyclic N,N-dialkylanilines as radical 1,3-bis radical donors. The success of this process relies on efficient electron transfer processes and highly selective deprotonation of aminium radical cations leading to the key α-amino radical intermediates.

Funder

Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung

Agence Nationale de la Recherche

LABoratoires d'EXcellence ARCANE

Publisher

Springer Science and Business Media LLC

Subject

Materials Chemistry,Biochemistry,Environmental Chemistry,General Chemistry

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